While there are a good number of individuals who regret attending law school, I don't regret my decision. I was very fortunate in the way that things played out.
Law school itself was as difficult as I thought. It’s essentially a tournament where you and your intelligent, hard-working classmates are competing for a finite number of good grades. Luckily, Penn is known for its collegiality, and I found all of my classmates to be good-natured, kind people.
As far as career opportunities, I was again lucky in that many recruiters visited Penn. Penn has a robust on-campus recruiting program which makes it easier for students to find jobs, especially at so-called “Big Law” firms. While I had to be a bit creative in my search, I received an offer to become a summer associate at a Big Law firm. After graduation, I became a full-time litigation associate at that same firm. I practiced at that firm for about two-and-a-half years before deciding to take a risk and start a company in New York City.
You’re right, however, that many people do regret attending law school. Often these regrets come from the fact that law school grads (1) can’t find a job in the legal industry; (2) are burdened with excessive debt that they cannot pay off; or (3) don’t enjoy legal practice.
A combination of (1) and (2) is deadly, and this is where you hear some horror stories (like law school grads becoming baristas at Starbucks). The best way to mitigate the risk of (1) is to attend a “prestigious” law school, especially one of the top 14 schools in the U.S. News & World Report law school rankings. You’ll be presented with more job opportunities and will have a greater chance of finding a job that inspired you to pursue law school in the first place.
As far as (2), debt is simply going to be a reality unless you obtain a scholarship and/or have financial backing from friends or family. The exact amount of debt will vary. That said, you’ll likely be paying off your loans for the foreseeable future. There are some programs that can help you—like the Public Service Loan Forgiveness Program—but you’ll still have to account for your debt years after law school.
Finally, one of the best ways to avoid (3) is to work in the legal industry before law school. Whether it’s an internship or a full-time position, you’ll get a better sense of whether you’re actually interested in legal practice. It’s not a comprehensive solution, but it’s better than nothing.